“Uhm… Steve, are you sure this is appropriate?” Cheryl asked with a little half smile on her lips and trepidation in her voice.
She’d just walked into my home office and cocked her hip to the side a little as she put her hand on her hip. I looked up from my computer screen and smiled warmly at her.
“Of course, it looks great!” I replied and she blushed a little in return.
“Well… if you’re sure…” she replied, still obviously not fully convinced but having a hard time saying anything else.
“Trust me, it’s perfect for the reunion.” I assured her and a little gasp escaped her lips and then a broad smile crossed them.
She nodded, then turned around and wiggled her ass as she left my office and headed back downstairs.
When she was out of ear shot I let out a soft chuckle and shook my head from side to side, it was going to be a great highschool reunion tonight… at least for me.
Cheryl had been one of the popular girls in highschool, aways dating the sports stars and flaunting her looks in skimpy outfits, while I had been one of the geeks, my nose buried in my keyboard and often ending up the brunt of Cheryl’s taunts.
When I’d graduated and headed off to college, Cheryl had stayed back in our small town with her highschool sweetheart, the football star. He never made it to college, blew out a knee in the last season, and their relationship deteriorated, and she stayed with him for several years after she should have left.
I on the other hand had started a very successful IT company, made a few million by the time I was 26, and sold it for a few billion a few years later. I’d returned to our small town, looking to give back to where I’d come from, brought my money and contacts, and invested in many of the small businesses that were struggling… including the restaurant where Cheryl was working as a waitress.
The first thing I did with any business I invested in was give it an IT revamp, and Cheryl’s restaurant was no exception. The new tablets they used to take orders were great at improving efficiencies, but were also a great way to deliver the subliminal message software I’d perfected in university.
Not that I’d needed it to get Cheryl to pay attention to me now, she had acted like we were best friends in highschool and started flirting with me right away. She view dating as a way to upgrade her lifestyle and I was the obvious choice to do it with.
The tablet, and later her own phone once I’d installed the software on it after a few dates, disabused her of that notion and replaced it with genuine trust and respect. Well trust, respect, and a new self image that was entirely tied to my opinion of her.
Like her question just a few moments ago, as much as she knew it was ridiculous for her to attend the reunion dressed up in a skimpy skirt, towering heels, and a top that showed off her tits, it didn’t matter. I’d said it was perfect, and so it was.
She was already primed to act like a complete bimbo tonight. Her responses to questions would amount to little more than giggles and “You should ask Steve… I’m sure he has an opinion on that” when one of the other well scripted responses didn’t quite fit.
The alert on my phone binged and I picked it up, it was the alarm I’d set to get ready for the reunion myself, so I locked my computer and headed to the bathroom to take a shower.
On my way by the staircase I saw Cheryl standing at the base of it, right by the front closet, holding a pair of much more sensible shoes. I paused for a moment and watched her head bob up and down, from her feet with the heels she was wearing now, to the shoes she was holding in her hands, then back and forth.
Finally she turned around and headed to the kitchen, a moment later I heard the garbage can open, the sensible shoes fall in, and then it close.
I wicked smile crossed my lips and I went straight to the shower. I already had the perfect spot picked out, just under the bleachers, where all the popular girls made out with their boyfriends back in the day. I couldn’t wait for the reunion to be over and I could take her back there, bent her over, and listened to her cry out my name as I finally took her anal cherry, the only cherry she had left for me to take.
